First Time
by CompletelyObsessive
Summary: Dan/ Blair AU story, from Dan's POV. Dan goes over the milestones in the Dair relationship. Apparently I should put a disclaimer- I don't own any rights to Gossip Girl


_We're both looking for something_

_We've been afraid to find_

_It's easier to be broken_

_It's easier to hide_

First Time- Lighthouse

I remember the first time I met Blair Waldorf at the bitter- sweet brunch on the Upper East Side. My hand still throbbed for punching Chuck Bass and I was falling in love with Serena Vanderwoodsen. A girl said my name, and although I had already been blinded by Serena's perfection, I could see Blair was beautiful. That was the girl that gave me my first dose of the ugliness that surrounded the Upper East Side, the last words that day she said to me being....

"I just wanted you to know, before you fall head over heels for your perfect girl in your perfect world and then get left all alone with no one but your cabbage patch kid."

She was everything I hated about the Upper East Side, distilled into one ninety five pound, dough- eyed, bon mot- tossing, label- whoring package of girlie evil. From that moment I knew Blair Waldorf was nothing more than a scheming bitch.

I remember the first moments I saw a different side to Blair Waldorf. The first, I had just been kicked off a fashion shoot and I was in Love with Serena Vanderwoodsen. I poured my heart out to this lonely girl who had just been betrayed by her best friend and her mother. The second time, Blair was clearly disgusted by our Brooklyn Art Gallery, and she was in love with Chuck Bass. She told me she was in love, and I could see a pain and longing deeper than her material Upper Class life. From that moment I knew Blair Waldorf's cunning was hiding a better person.

I remember the first time I kissed Blair Waldorf. I realized at the moment that I knew nothing about that girl.

---------------

It started with a friendship, a rocky one at best, that was formed for the wreckage that was our late teenage lives. My writing career was over, and my chase for Vanessa had given me nothing but heartbreak. Blair couldn't be queen of the Upper East Side or NYU, and the inevitable had happened. Chuck and Blair had broken up, I only knew that it was the doing of Jack Bass. College was all we had left so when I needed something to hold onto from my high school life, it was Blair I grabbed onto with both hands, and she didn't make me let go. It started with plots and schemes, which eventually led to coffee and chats, despite all odds and differences. But the next step truly started that night…

I was reading in the dim light of a cheap lamp bought with my own money, I managed to keep the last bit of dignity I had left by buying my own possessions despite the riches Rufus had now. I groaned and answered my bedroom door after a sharp knock announced the arrival of none other than Blair Waldorf, who in her usual manner entered as soon as the door was unlocked.

"Always a pleasure Blair," I said sarcastically

"If it isn't Brooklyn's sharpest mind," she replied, a small smile on her red lips. And I couldn't help but smile back.

"Anyway now the pleasantries are out of the way…"

I interrupted Blair with a snort and a murmur of 'pleasantries', but she just smoothed her already perfect yellow strappy top before continuing.

"… ahem, well, here you go Humphrey."

Blair thrust a magazine into my chest with a perfectly manicured hand, then, if I hadn't have known better, appeared to look away in embarrassment.

"Wow," I said in a monotone, "Its an old copy of the New Yorker."

Blair sighed impatiently at me and flicked to a page in the magazine before handing it back. "Not just any 'old copy', it's the august of 2008 edition, you said you'd lost yours."

It took me a few seconds a a blank stare later to realise what she had given me. "My article! You remembered that?"

"Of course." Blair said quietly than shifted uncomfortably at the silence that followed.

I had neglected to tell her that Rufus and Lily had about ten framed copies, but that didn't matter. What mattered was that Blair Waldorf, even with all her money, got me a gift that cost less than $100, and it actually meant something. I opened my mouth to try and thank her, but didn't know what to say. Even after our short friendship I could not deny that Blair was just as manipulative as ever. But now.

_Looking at you, holding my breath_

_For once in my life I'm scared to death_

_I'm taking a chance letting you inside_

"Well I have to be…."

Blair didn't get to finish her sentence before the gap between us was closed and my lips were pressed against hers, for a moment unmoving. My head was bent to her level, and my free hand held her cheek. It was crazy I knew, Blair Waldorf and Dan Humphrey was an impossible sentence. But she kissed me back. My head could not recognise the situation, but it didn't want to. The kiss didn't feel like Serena's or Vanessa's, I only remember love and friendship from their lips. This was something different, like we both knew that the pathetic excuse for a friendship we had would lead to this. Blair grabbed my collar, pulling me closer to her body, and the hand I had rested on her cheek got tangled in beautiful wavy hair. I could fell a heat already radiating from the petite brunette as our lips moved in a fury of confusion and passion and her chest pressed against mine. Her hands crept into my hair, and in response I wrapped my free arm around her waist, dropping the New Yorker at our feet. But just like that, the thud of the magazine seemed to break the joke of a spell. Blair unwrapped herself from me, pushing me away lightly, as she realised what had just happened. Her hair fell around her face and framed its pale beauty as she shook her head in shock and confusion. And with one last look at me from her deep brown eyes, Blair rushed from my dorm. Every step she took in her heels echoed down the hall, and for some impossible reason every step struck me like a knife.

I remember the first time I kissed Blair Waldorf. An old magazine sat on my bedroom floor, and I didn't know who I loved anymore. Was Blair, this beautiful complicated girl, thinking about me as she went back to her room that night, was she thinking about Chuck or Serena as we kissed? My head was full of tales of a princess who's heart had been broken so many times by a dark prince, and she had to be saved. I tired to sleep that night but I couldn't and I knew from that moment that I was falling in Love with Blair Waldorf.

_I'm taking a chance letting you inside_.


End file.
